Dye complex and optical information recording medium

Details Dye complex and optical information recording medium Dye complex and optical information recording medium

2001-04-06

2003-01-14

Angebranndt, Martin (Department: 1756)

Radiation imagery chemistry: process, composition, or product th

Imaging affecting physical property of radiation sensitive...

Radiation sensitive composition or product or process of making

C430S270160, C430S270210, C430S270200, C430S945000, C428S064800, C428S913000, C552S303000, C552S307000, C552S309000, C552S310000, C558S044000, C558S055000

Reexamination Certificate

active

06506539

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to a dye complex and an optical information recording medium of heat mode type on which information can be recorded by means of a laser beam. Further, the invention relates to a novel water-soluble tetracyanoquinodimethane derivative. Furthermore, the invention relates to novel cyanine dyes which are favorably employable as material of a recording layer of a heat more optical information recording medium.
BACKGROUND OF THE INVENTION
An information recording medium on which information can be recorded by means of a laser beam is known as a recordable compact disc (CD-R) or a recordable digital versatile disc (DVD-R).
The recordable optical disc generally has a multi-layer structure typically comprising a disc-shaped transparent substrate (support), a recording layer comprising an organic dye, a light-reflecting metal layer, and a resinous protective layer overlaid in order.
The recordable optical disc is desired to have high light-resistance after recording, high sensitivity and high information reproductivity.
It is known that a tetracyanoquinodimethane (TCNQ) or a derivative thereof can enhance the light-resistance of the recording dye layer when it is incorporated into the dye layer.
U.S. Pat. No. 5,579,150 describes an optical recording medium using a charge transfer complex of cyanine-TCNQ.
TCNQ and derivatives thereof are also employable as electron acceptors of charge transfer complexes for preparing organic electroconductive materials.
It is an object of the present invention to provide a complex comprising a dye cation and a anionic tetracyanoquinodimethane derivative which is easily dissolved in various polar solvents and further shows increased light-resistance and therefore which is favorably employable for preparing a recording dye layer of a recordable optical medium.
It is another object of the invention to provide an optical information recording medium having a recording dye layer which shows increased light-resistance and a high sensitivity.
It is a further object of the invention to provide novel water-soluble tetracyanoquinodimethanes which are favorably employable as electron acceptors.
It is a further object of the invention to provide novel cyanine dye cations which show a high sensivitity in a wide wavelength range.
SUMMARY OF THE INVENTION
The present invention resides a complex comprising a dye cation and an anionic tetracyanoquinodimethane derivative having the following formula (I):
in which [Dye]
+
represents a dye cation, L
1
is a linking group containing at least one methylene group, R
1
is a substituent group, p is an integer of 1 to 4, and r is an integer of 0 to 3 under the condition of 1<p+r<4, provided that a cationic charge of the dye cation and an anionic charge of the anionic tetracyanoquinodimethane derivative are adjusted to make the complex neutral.
In the formula (I), the group of —L
1
—SO
3
— is preferably represented by the formula of —O—R
2
—O—L
2
—SO
3
— or —O—R
2
—OSO
3
— in which R
2
is an alkylene group which may have one or more substituent groups, and L
2
is a divalent linking group.
In the complex of the formula (I), the dye cation preferably is a dye cation having the following formula (II):
wherein each of A
1
and A
2
independently represents a benzene or naphthalene ring which has no substituent group or which has one or more substituent groups, n is an integer of 0 to 2, each of R
3
and R
4
independently represents a hydrogen atom, an alkyl group, an aralkyl group, or a heterocyclic group, and each of R
5
, R
6
, R
7
and R
8
independently represents an alkyl group which has no substituent group or has one or more substituent groups, provided that the methine group has no substituent group or has one or more substituent groups.
The present invention further resides in an optical information recording medium comprising a substrate and a recording layer on which information is recordable by irradiation with a laser beam, wherein said recording layer comprises a complex of a dye cation and an anionic tetracyanoquinodimethane derivative having the aforementioned formula (I).
The present invention further resides in a complex of a cation and an anionic tetracyanoquinodimethane derivative having the following formula (IX):
in which [CI]
+
represents a cation, R
1
is a substituent group, R
2
is an alkylene group which has one or more substituent groups or has no substituent groups, L
2
is a single bond or a divalent linking group, p is an integer of 1 to 4, and r is an integer of 0 to 3 under the condition of 1<p+r<4, provided that a cationic charge of the cation and an anionic charge of the anionic tetracyanoquinodimethane derivative are adjusted to make the complex neutral.
The invention furthermore resides in cationic cyanine dye/anion complexes having one of the following formulas (III) to (VIII):
in which n is 0, 1 or 2, R
3
represents a hydrogen atom, an alkyl group containing 1 to 6 carbon atoms, or an aralkyl group having an alkyl moiety of 1 to 3 carbon atoms, R
4
represents a hydrogen atom, each of R
5
, R
6
, R
7
and R
8
represents a methyl group, and each of R
9
and R
10
independently represents a hydrogen atom, an alkyl group containing 1 to 6 carbon atoms, a halogen atom, or an alkoxy group containing 1 to 6 carbon atoms, provided that where n is 1 or 2, alkyl, halogen, methoxy, phenyl or 4-pyridyl can be attached to a meso position at the center of the methine chain;
in which n is 0, 1 or 2, R
3
represents a hydrogen atom, an alkyl group containing 1 to 6 carbon atoms, or an aralkyl group having an alkyl moiety of 1 to 3 carbon atoms, R
4
represents a hydrogen atom, each of R
5
, R
6
, R
7
and R
8
represents a methyl group, and each of R
9
and R
10
independently represents a hydrogen atom, an alkyl group containing 1 to 6 carbon atoms, a halogen atom, or an alkoxy group containing 1 to 6 carbon atoms, provided that where n is 1 or 2, alkyl, halogen, methoxy, phenyl or 4-pyridyl can be attached to a meso position at the center of the methine chain;
in which n is 0, 1 or 2, each of R
3
and R
4
independently represents a hydrogen atom, an alkyl group containing 1 to 6 carbon atoms, or an aralkyl group having an alkyl moiety of 1 to 3 carbon atoms, and each of R
5
, R
6
, R
7
and R
8
represents a methyl group, provided that where n is 1 or 2, alkyl, halogen, methoxy, phenyl or 4-pyridyl can be attached to a meso position at the center of the methine chain, where n is 1, there is no case where both of R
3
and R
4
are methyl, and where n is 2, at least one of R
3
and R
4
is hydrogen;
in which n is 0, 1 or 2, each of R
3
and R
4
independently represents a hydrogen atom, an alkyl group containing 1 to 6 carbon atoms, or an aralkyl group having an alkyl moiety of 1 to 3 carbon atoms, each of R
5
, R
6
, R
7
and R
8
represents a methyl group, and R
10
represents a hydrogen atom, an alkyl group containing 1 to 6 carbon atoms, a halogen atom, or an alkoxy group containing 1 to 6 carbon atoms, provided that where n is 1 or 2, alkyl, halogen, methoxy, phenyl or 4-pyridyl can be attached to a meso position at the center of the methine chain;
in which n is 0, 1 or 2, each of R
3
and R
4
independently represents a hydrogen atom, an alkyl group containing 1 to 6 carbon atoms, or an aralkyl group having an alkyl moiety of 1 to 3 carbon atoms, each of R
5
, R
6
, R
7
and R
8
represents a methyl group, and each of R
9
and R
10
independently represents a hydrogen atom, an alkyl group containing 1 to 6 carbon atoms, a halogen atom, or an alkoxy group containing 1 to 6 carbon atoms, provided that where n is 1 or 2, alkyl, halogen, methoxy, phenyl or 4-pyridyl can be attached to a meso position at the center of the methine chain, and where both of R
9
and R
10
are hydrogen, at least one of R
3
and R
4
is hydrogen;
in which n is 0, 1 or 2, each of R
3
and R
4
independently represents a hydrogen atom, an alkyl group containing 1 to 6 carbon atoms, or an aralkyl group having an

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